Wildwood Trail (multiple options)1 of 7
This 30-mile-long trail winds through 40,000 acres of open space running from Washington Park to Northwest Newberry Road. You can access different parts of the trail throughout Washington Park for various loops to suit any activity level (and plenty of options to circle back to the park for a picnic, napping or ice cream). The trailhead at the old Pittock Mansion site is a great starting spot as it meanders along a river from Pittock Acres Park. Keep in mind this hike is downhill in one direction—so be prepared to carry any tired little ones with you on the way back.
Washington Park2 of 7
Washington Park is a central destination for families as its home to a number of attractions including the Oregon Zoo, The Rose Garden, The Portland Japanese Gardens and Hoyt Arboretum. Grab a map at the entrance to the arboretum and head out on the museum's trails (there are more than 12 miles of them) for an educational and awe-inspiring stroll under forest canopy home to the largest group of distinct species of any U.S. living museum.
The 4T Trail3 of 7
This one-of-a-kind trail incorporates walking with tram, trolley and train riding--a sure delight for any child. The trail starts just past the Oregon Zoo as you make the short (but steep!) hike up to Council Crest Park before heading down to the Oregon Health and Science University. There, you'll board the Portland Aerial Tram as you glide down 3,300 linear feet to the water's edge. Once at sea level, you'll board the Portland Streetcar for a fun-filled ride to downtown Portland.
Grab a bite at one of downtown's famous food trucks before hopping on the MAX light rail train back to the zoo. The whole loop takes about four hours and includes roughly four miles of walking, so it might be best to bring along a stroller or carrier for especially little legs.
Mt. Tabor Park4 of 7
Located near Hawthorne—an of-the-moment hipster neighborhood filled with vintage shops and local eateries—this park is home to an extinct volcano; that fact alone might induce some "whoa!" moments from the little ones. The area's steep slopes are filled with trails that wind all the way up to the top of Mt. Tabor, at which point you'll be rewarded with views of the entire city.
Tryon Creek State Natural Area5 of 7
With more than 650 acres of second-growth forests, wildflowers, creeks and hundreds of species of Pacific Northwest wildlife, this gem of a park located just 15 minutes from downtown Portland should be on any outdoorsy family's must-visit list. There are more than eight miles of hiking trails, a flat, paved three-mile bicycle trail and a fantastic nature center with interesting interpretive exhibits. Start out on the half-mile-long Maple Ridge Trail, which leaves from the Nature Center, and if you're little ones are up to it you can connect with the Middle Creek Trail and head all the way to Tryon Creek.
Maricara Natural Area6 of 7
Photo Credit: Portland Parks & Recreation, Portland, OR
Known as the little brother park to nearby Tryon Creek in Southwest Portland, this nature preserve offers nearly 20 acres of flat, forested wetland trail options perfect for little feet to explore (and get muddy!). The main trailhead is located near SW 30th Avenue in the Markham neighborhood, and due to a lack of street parking is best accessed by bike or public transportation.